# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p
_database_code_depnum_ccdc_archive 'CCDC 1522514'
_audit_update_record             
;
2016-12-13 deposited with the CCDC.
2017-02-23 downloaded from the CCDC.
;
_audit_creation_date             2016-03-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '8(C32 H34 B Br2 N)'
_chemical_formula_sum            'C114 H0 B94 Br16 N64'
_chemical_formula_weight         4560.48
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   8.3209(7)
_cell_length_b                   16.6734(14)
_cell_length_c                   42.266(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5863.9(8)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4592
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.331
_cell_measurement_theta_min      2.627
_exptl_absorpt_coefficient_mu    2.783
_exptl_absorpt_correction_T_max  0.7683
_exptl_absorpt_correction_T_min  0.6803
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2162
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            31501
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.62
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71000
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3396
_reflns_number_total             5158
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.796
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         5158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0505
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0420P)²+9.4915P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1236
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C8(H8), C9(H9), C11(H11), C18(H18), C21(H21),
 C27(H27), C30(H30)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C20(H20A,H20B,
 H20C), C23(H23A,H23B,H23C), C26(H26A,H26B,H26C), C29(H29A,H29B,H29C), C32(H32A,
 H32B,H32C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Br1 Br 0.70254(10) 0.28293(6) 0.497048(13) 0.1254(4) Uani 1 d . . .
Br2 Br 0.65234(7) 0.39881(3) 0.747968(11) 0.0716(2) Uani 1 d . . .
N1 N 0.3707(4) 0.3945(2) 0.59330(8) 0.0502(9) Uani 1 d . . .
C1 C 0.6822(7) 0.3104(3) 0.54053(10) 0.0653(14) Uani 1 d . . .
C2 C 0.8085(6) 0.2994(3) 0.55996(11) 0.0639(13) Uani 1 d . . .
H2 H 0.9059 0.2797 0.5525 0.077 Uiso 1 calc . . R
C3 C 0.7874(5) 0.3186(3) 0.59157(10) 0.0543(12) Uani 1 d . . .
H3 H 0.8738 0.3125 0.6053 0.065 Uiso 1 calc . . R
C4 C 0.6423(5) 0.3465(2) 0.60363(8) 0.0381(9) Uani 1 d . . .
C5 C 0.5164(5) 0.3613(2) 0.58242(9) 0.0431(10) Uani 1 d . . .
C6 C 0.5386(6) 0.3421(3) 0.55069(10) 0.0594(13) Uani 1 d . . .
H6 H 0.4560 0.3509 0.5363 0.071 Uiso 1 calc . . R
C7 C 0.6333(4) 0.3574(2) 0.63885(9) 0.0354(9) Uani 1 d . . .
C8 C 0.7277(5) 0.4178(2) 0.65186(10) 0.0449(10) Uani 1 d . . .
H8 H 0.7883 0.4502 0.6385 0.054 Uiso 1 calc . . R
C9 C 0.7336(5) 0.4308(2) 0.68408(10) 0.0472(11) Uani 1 d . . .
H9 H 0.7978 0.4713 0.6924 0.057 Uiso 1 calc . . R
C10 C 0.6431(5) 0.3831(2) 0.70357(9) 0.0408(10) Uani 1 d . . .
C11 C 0.5472(4) 0.3236(2) 0.69133(9) 0.0367(9) Uani 1 d . . .
H11 H 0.4853 0.2929 0.7051 0.044 Uiso 1 calc . . R
C12 C 0.5397(4) 0.3080(2) 0.65885(8) 0.0318(8) Uani 1 d . . .
C13 C 0.3842(6) 0.4732(3) 0.60864(12) 0.0665(14) Uani 1 d . . .
H13A H 0.4652 0.4709 0.6248 0.100 Uiso 1 calc . . GR
H13B H 0.2829 0.4873 0.6180 0.100 Uiso 1 calc . . GR
H13C H 0.4135 0.5128 0.5932 0.100 Uiso 1 calc . . GR
C14 C 0.2361(6) 0.3953(4) 0.57063(12) 0.0783(16) Uani 1 d . . .
H14A H 0.1399 0.4122 0.5812 0.117 Uiso 1 calc . . GR
H14B H 0.2210 0.3425 0.5622 0.117 Uiso 1 calc . . GR
H14C H 0.2599 0.4319 0.5537 0.117 Uiso 1 calc . . GR
C15 C 0.7709(5) 0.1562(3) 0.64310(11) 0.0578(12) Uani 1 d . . .
H15A H 0.8192 0.1054 0.6480 0.087 Uiso 1 calc . . GR
H15B H 0.7214 0.1778 0.6618 0.087 Uiso 1 calc . . GR
H15C H 0.8520 0.1926 0.6357 0.087 Uiso 1 calc . . GR
C16 C 0.4899(4) 0.1773(2) 0.62009(8) 0.0335(9) Uani 1 d . . .
C17 C 0.6457(5) 0.1450(2) 0.61780(9) 0.0443(10) Uani 1 d . . .
C18 C 0.6874(6) 0.0978(3) 0.59173(10) 0.0562(12) Uani 1 d . . .
H18 H 0.7902 0.0762 0.5907 0.067 Uiso 1 calc . . R
C19 C 0.5810(7) 0.0825(3) 0.56758(11) 0.0613(13) Uani 1 d . . .
C20 C 0.6319(8) 0.0333(4) 0.53904(13) 0.104(2) Uani 1 d . . .
H20A H 0.6360 -0.0224 0.5447 0.156 Uiso 1 calc . . GR
H20B H 0.7363 0.0505 0.5321 0.156 Uiso 1 calc . . GR
H20C H 0.5558 0.0407 0.5222 0.156 Uiso 1 calc . . GR
C21 C 0.4287(6) 0.1129(3) 0.57035(10) 0.0559(12) Uani 1 d . . .
H21 H 0.3552 0.1025 0.5543 0.067 Uiso 1 calc . . R
C22 C 0.3792(5) 0.1584(2) 0.59604(9) 0.0405(10) Uani 1 d . . .
C23 C 0.2089(5) 0.1872(3) 0.59720(11) 0.0565(12) Uani 1 d . . .
H23A H 0.1564 0.1747 0.5776 0.085 Uiso 1 calc . . GR
H23B H 0.2075 0.2442 0.6005 0.085 Uiso 1 calc . . GR
H23C H 0.1536 0.1612 0.6143 0.085 Uiso 1 calc . . GR
C24 C 0.2896(4) 0.2091(2) 0.66995(8) 0.0340(9) Uani 1 d . . .
C25 C 0.1659(5) 0.2644(2) 0.67644(9) 0.0381(9) Uani 1 d . . .
C26 C 0.1668(5) 0.3481(2) 0.66271(11) 0.0529(11) Uani 1 d . . .
H26A H 0.2306 0.3826 0.6759 0.079 Uiso 1 calc . . GR
H26B H 0.0588 0.3682 0.6617 0.079 Uiso 1 calc . . GR
H26C H 0.2118 0.3467 0.6418 0.079 Uiso 1 calc . . GR
C27 C 0.0374(5) 0.2432(3) 0.69542(9) 0.0454(10) Uani 1 d . . .
H27 H -0.0432 0.2807 0.6991 0.055 Uiso 1 calc . . R
C28 C 0.0250(5) 0.1684(3) 0.70900(9) 0.0489(11) Uani 1 d . . .
C29 C -0.1148(6) 0.1485(4) 0.73062(12) 0.0797(16) Uani 1 d . . .
H29A H -0.1239 0.0914 0.7327 0.120 Uiso 1 calc . . GR
H29B H -0.2123 0.1696 0.7218 0.120 Uiso 1 calc . . GR
H29C H -0.0968 0.1719 0.7511 0.120 Uiso 1 calc . . GR
C30 C 0.1448(5) 0.1139(3) 0.70272(9) 0.0487(11) Uani 1 d . . .
H30 H 0.1383 0.0631 0.7117 0.058 Uiso 1 calc . . R
C31 C 0.2754(5) 0.1318(2) 0.68342(9) 0.0387(9) Uani 1 d . . .
C32 C 0.4047(6) 0.0693(2) 0.67988(11) 0.0567(12) Uani 1 d . . .
H32A H 0.4165 0.0556 0.6579 0.085 Uiso 1 calc . . GR
H32B H 0.3755 0.0223 0.6917 0.085 Uiso 1 calc . . GR
H32C H 0.5045 0.0901 0.6878 0.085 Uiso 1 calc . . GR
B1 B 0.4382(5) 0.2322(2) 0.64853(10) 0.0327(10) Uani 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.902(4) . ?
Br2 C10 1.896(4) . ?
N1 C5 1.409(5) . ?
N1 C13 1.468(6) . ?
N1 C14 1.474(5) . ?
C1 C2 1.346(7) . ?
C1 C6 1.375(6) . ?
C2 C3 1.385(6) . ?
C3 C4 1.391(5) . ?
C4 C5 1.401(5) . ?
C4 C7 1.501(5) . ?
C5 C6 1.391(6) . ?
C7 C8 1.391(5) . ?
C7 C12 1.413(5) . ?
C8 C9 1.380(5) . ?
C9 C10 1.370(5) . ?
C10 C11 1.374(5) . ?
C11 C12 1.399(5) . ?
C12 B1 1.581(5) . ?
C15 C17 1.505(6) . ?
C16 C17 1.408(5) . ?
C16 C22 1.407(5) . ?
C16 B1 1.570(5) . ?
C17 C18 1.397(5) . ?
C18 C19 1.375(6) . ?
C19 C20 1.519(6) . ?
C19 C21 1.369(7) . ?
C21 C22 1.388(6) . ?
C22 C23 1.497(6) . ?
C24 C25 1.409(5) . ?
C24 C31 1.414(5) . ?
C24 B1 1.580(6) . ?
C25 C26 1.511(5) . ?
C25 C27 1.382(5) . ?
C27 C28 1.377(6) . ?
C28 C29 1.516(6) . ?
C28 C30 1.375(6) . ?
C30 C31 1.391(6) . ?
C31 C32 1.505(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C13 115.4(3) . . ?
C5 N1 C14 116.4(4) . . ?
C13 N1 C14 109.7(4) . . ?
C2 C1 Br1 119.2(4) . . ?
C2 C1 C6 122.7(4) . . ?
C6 C1 Br1 118.2(4) . . ?
C1 C2 C3 117.3(4) . . ?
C2 C3 C4 122.8(4) . . ?
C3 C4 C5 118.3(4) . . ?
C3 C4 C7 116.6(3) . . ?
C5 C4 C7 125.2(3) . . ?
C4 C5 N1 120.2(3) . . ?
C6 C5 N1 121.3(4) . . ?
C6 C5 C4 118.5(4) . . ?
C1 C6 C5 120.3(4) . . ?
C8 C7 C4 116.8(3) . . ?
C8 C7 C12 119.8(3) . . ?
C12 C7 C4 123.4(3) . . ?
C9 C8 C7 121.6(4) . . ?
C10 C9 C8 118.8(4) . . ?
C9 C10 Br2 119.5(3) . . ?
C9 C10 C11 120.8(4) . . ?
C11 C10 Br2 119.7(3) . . ?
C10 C11 C12 122.0(4) . . ?
C7 C12 B1 126.5(3) . . ?
C11 C12 C7 117.0(3) . . ?
C11 C12 B1 116.3(3) . . ?
C17 C16 B1 121.8(3) . . ?
C22 C16 C17 117.9(3) . . ?
C22 C16 B1 120.3(3) . . ?
C16 C17 C15 122.8(4) . . ?
C18 C17 C15 117.3(4) . . ?
C18 C17 C16 119.9(4) . . ?
C19 C18 C17 122.0(4) . . ?
C18 C19 C20 120.7(5) . . ?
C21 C19 C18 117.6(4) . . ?
C21 C19 C20 121.7(5) . . ?
C19 C21 C22 123.0(4) . . ?
C16 C22 C23 121.6(4) . . ?
C21 C22 C16 119.6(4) . . ?
C21 C22 C23 118.8(4) . . ?
C25 C24 C31 117.2(3) . . ?
C25 C24 B1 121.6(3) . . ?
C31 C24 B1 121.2(3) . . ?
C24 C25 C26 121.7(3) . . ?
C27 C25 C24 120.7(4) . . ?
C27 C25 C26 117.6(4) . . ?
C28 C27 C25 122.1(4) . . ?
C27 C28 C29 120.5(5) . . ?
C30 C28 C27 117.6(4) . . ?
C30 C28 C29 121.9(4) . . ?
C28 C30 C31 122.6(4) . . ?
C24 C31 C32 122.1(4) . . ?
C30 C31 C24 119.8(4) . . ?
C30 C31 C32 117.9(4) . . ?
C16 B1 C12 122.0(3) . . ?
C16 B1 C24 120.7(3) . . ?
C24 B1 C12 117.0(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
